1. Field of the Invention
The present invention relates to a new composition and a novel process to prepare or produce such compositions as well as analogous ones.
More particularly, the present invention relates to a new composition and a novel process to prepare or produce such compositions, where the composition includes a hydrophilic part and a hydrophobic part that is suitable for use as a detergent, a surfactant or an emusilfier component, and for the construction of cellular membranes or any membrane or organic film. The compositions are neutral, where the hydrophilic part and hydrophobic part are connected through at least an amide bond or an ester bond. The process to produce the compositions is a novel chemical reaction between a carbohydrate, or acyl group or ether group protected carbohydrate and any of nitrites containing long or short hydrocarbon chains; with or without branching; either saturated or unsaturated; with or without cyclic or aromatic ring. This process uses an acid to promote the conversion rate with or without a salt from group IB metal. The process to produce such composition of matter can undergo in an inert solvent or without any solvent in presence. The process uses a high speed mixing equipment.
2. Description of the Related Art
Surfactants or so-called surface active agents, are types of molecules that can reduce the surface tension of water or other molecules, and can used as detergents, emulsifiers, etc. By chemical definition molecules that are surfactants are molecules that structurally possess a hydrophilic (or lipophobic) component and a hydrophobic (or lipophilic) component. [1] In general the properties of surfactants fall into two broad categories: adsorption and aggregation (or self-assembly). [2] The adsorption properties of surfactants are those that allow the surfactant molecules to be found at the interface between immiscible or only slightly miscible phases such as an oil phase and a water phase, or a water phase and an air phase. It is this latter molecular property that leads to the macroscopic properties possessed by the surfactant such as wetting, foaming, detergency and emulsification. [3] In contrast, aggregation or self-assembly is the tendency for surfactant molecules to organize themselves into extended structures in water. This includes the formation, for example, of micelles, bilayers, liposome and liquid crystals etc. [4] These structures are formed when the hydrophobic parts of surfactants cluster together. When the hydrophilic component is larger than the lipophilic component, micelles are likely to form; by comparison, if the size of hydrophilic component is comparable to the size of the lipophilic component, then bilayers, liposome and membrane structures will form. [5]
The hydrophobic component of commonly used surfactants is long hydrocarbon chains containing between 4 to 20 carbons. An increase in the number of carbons beyond 20 usually has associated with its higher toxicity. [6] By contrast, the hydrophilic component of a surfactant can be either polar or carry a charge (positive or negative or amphoteric). Consequently, surfactants are usually classified into one of four general categories: cationic surfactants, anionic surfactants, neutral or nonionic surfactants, and amphoteric surfactants. The cationic surfactants have a positive charge on the head group when dissolved in water, for example, the carrying of a positively charged ammonium pendent; anionic surfactants will have negatively charged groups as head groups when dissolving in water, (e.g., a sulfate, phosphate, or carboxylate group etc.); nonionic surfactants can have either polyethylene glycols or carbohydrates as polar head groups, and amphoteric surfactants can have positive charges and weak bascity or vice versa. Surfactants, when used as detergents, can form micelles and engulf grease, or oily stains from commonly used clothing materials, so that they can be washed away from the clothes. Similarly, when surfactants are used as emusilfiers, they accumulate on the oil/water interface and prevent coalescing of oil droplets. These emulsifiers can create and maintain the thereby formed emulsions for hours (e.g., salad dressing), months, or years (e.g., medicinal or cosmetic cream). [7]
It is known that long-term exposure to anionic surfactants has been linked to swelling of the skin and skin irritation. Therefore, it is common to add alkyldimethylamine oxide, which is known to depress skin irritation factors, to anionic surfactants. [8] Because, or in spite of this need during manufacture of anionic surfactants, anionic surfactants are generally avoided in cosmetic products. Cationic surfactants are typically used in things like hair-conditioner and fabric softeners. [9] The fatty amine salts proved quite useful in blends with nonionic surfactants, giving good stability over a range of pH levels. Cationic surfactants are generally rated as being more irritating to the skin than anionic surfactants, probably because of their strong ability to adsorb to negatively charged materials on skin, such as proteins and nucleic acid [10] and the cationic surfactants are also not biodegradable. [9] In contrast, the nonionic surfactants are more user friendly, and have much fewer problems with respect to allergic reactions or skin irritation. Thus, the latter type of surfactants are ubiquitous in foods and drinks as well as pharmaceuticals and skin-care products. [11] It is believed that these surfactants have mild negative effects on the skin even at high loading concentrations and long-term exposure. It is because of such features, that the nonionic surfactants are getting more and more use in current processes that demand surfactants. This is especially true for those type of nonionic surfactants that originate from carbohydrates.
Carbohydrate-containing surfactants fall into three distinctly different classes: esters, acetals and amides, and examples of these such as the alkyl glucamides, were not commercialized until the 1990s. [12] Currently, alkyl sugar-amides are manufactured in two steps: reductive amination of a carbohydrate with an alkylamine, followed by the acylation of the resulting N-glycosides; [13] similarly, gluconamides, the “reverse glucamides” are also produced in two steps: the oxidation of a carbohydrate leading to lactone or aldonic acid followed by reaction with alkyl amines to form gluconamides. [14] In both processes opening of the carbohydrate ring occurs. However, a carbohydrate-containing nonionic surfactant with an amide linkages to the ring of carbohydrate through a N-glycosidic bond, without opening of the carbohydrate ring is neither known, or suggested in the literature.
Since the aforementioned type of nonionic surfactants have the amide bond linking the hydrophilic and lipophilic components via a N-glycosidic bond, it would be much easier to biodegrade than, for example, alkylpolyglucosides and probably also much more susceptible to biodegradation that either the alkyl glucamides or aldonamides as well. The amide bond in this new structural type of surfactant can be also digested by enzymes currently used in detergent formulation, in a manner similar to the degradation of other proteins by those enzymes. In addition, the biodegradation components from this type of novel surfactants are essentially carbohydrates and fatty acids, both of which are tolerable to humans, animals and the environment. This new type of surfactants have even an advantage over the currently used glucamides surfactants, since the glucamides surfactants will give N-glycosides after degradation of the amide bond, a product which is not easily biodegradable. Therefore, the new surfactants are much more mild and user friendly.
Accordingly, there is a need for such a composition of matter for surfactants, that can be used in detergents, pharmaceutical, medicinal, cosmetics and food industry, and a process to produce such compositions of matter in an efficient and high yield fashion.